Selective fluorescence-based detection of dihydrouridine with boronic acids

The first fluorescent sensing system for dihydrouridine detection is presented. Dihydrouridine is the single most frequently occurring post-transcriptional modification in tRNA from bacteria and eukaryotes. A series of 10 boronic acid derivatives was prepared and their fluorogenic behaviours towards dihydrouridine and uridine were investigated. Whereas uridine always quenches fluorescence via π–π stacking interactions, several boronic acid sensors have been found to show substantial fluorescence enhancement upon binding with dihydrouridine.